Secnidazole

Breast Feeding; Lactation; Anti-Infective Agents; Antiprotozoal Agents; Nitroimidazoles

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

135.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

133.76 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

138.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

This chemical does not meet GHS hazard criteria for 22.2% (2 of 9) of reports.

Warning

H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 9 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Secnidazole is typically given as a single oral dose and, in follow up, de novo serum enzyme elevations occur rarely, overall rates being less than 0.5% of participants. In prelicensure studies, there were no reported cases of clinically apparent liver injury. Furthermore, despite considerable use worldwide, secnidazole has not been linked convincingly to instances of clinically apparent liver injury with jaundice.

Drug Induced Liver Injury Rank (DILIrank 2.0)

Secnidazole

Ambiguous-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

P01AB07

P - Antiparasitic products, insecticides and repellents

Secnidazole is a broad-spectrum nitroimidazole antimicrobial drug. It is selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. According to _in vitro_ studies, secnidazole mediates antibacterial effects against _Bacteroides fragilis_, _Trichomonas vaginalis_, _Entamoeba histolytica_, and _Giardia lamblia_. Secnidazole may prolong the QTc interval, but not to a clinically significant extent.

Like other 5-nitroimidazole antimicrobials, the antimicrobial and antiprotozoal activity of secnidazole is accounted for by the nitro group in the imidazole ring. Upon entering the target pathogen, the nitro group of secnidazole is reduced by bacterial or parasitic nitroreductase enzymes, producing radical anions and reactive intermediates. Radical anions and reactive intermediates cause the depletion of thiols, DNA helix damage, disruption of bacterial or parasitic protein synthesis and replication, and ultimately, cell death of susceptible isolates of Gram positive bacteria, Gram negative bacteria and _T. vaginalis_.

The metabolism of secnidazole has not been fully characterized. According to _in vitro_ studies, secnidazole is metabolized by hepatic CYP450 enzymes, with less than or equal to 1% of the parent drug converted to metabolites. Secnidazole was found to be metabolized by CYP3A4 and CYP3A5 but to a limited extent. Secnidazole most likely undergoes oxidation. A hydroxymethyl metabolite and glucuronide conjugates of secnidazole have been detected in urine.